CN104650157A - Synthesis method and application of a complex [Ni(H2L2)2](H2O)2 with anticancer activity - Google Patents
Synthesis method and application of a complex [Ni(H2L2)2](H2O)2 with anticancer activity Download PDFInfo
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- CN104650157A CN104650157A CN201510071798.3A CN201510071798A CN104650157A CN 104650157 A CN104650157 A CN 104650157A CN 201510071798 A CN201510071798 A CN 201510071798A CN 104650157 A CN104650157 A CN 104650157A
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- title complex
- analytically pure
- synthesis method
- amino
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Abstract
The invention discloses a synthesis method and application of a complex [Ni(H2L2)2](H2O)2 with anticancer activity. [Ni(H2L2)2](H2O)2 has the molecular formula of C26H40N2NiO10 and the molecular weight of 599.29. The synthesis method comprises the steps of (1) mixing 1.662g of analytically pure ethoxysalicylaldehyde and 15ml of absolute ethyl alcohol, adding 1.051g of analytically pure 2-amino-2-methyl-1,3-propanediol and 10ml of absolute ethyl alcohol, heating, carrying out reflux stirring, cooling, crystallizing and standing to obtain H3L2 (H3L2=2-((3-ethyoxyl-2-hydroxybenzylidene)amino)-2-methyl-1,3-propanediol; (2) dissolving 0.128g of H3L2 and 0.249g of analytically pure nickel acetate tetrahydrate into 15-20ml of a mixed solution of absolute ethyl alcohol and self-made distilled water which are in the volume ratio of 5:5; and (3) transferring the mixed solution to a reaction kettle, reacting, cooling, filtering and crystallizing. [Zn(H2L2)2](H2O)5 can be applied as an anticancer drug. The synthesis method is simple in process, low in cost, good in repeatability and high in yield; and chemical components are easily controlled.
Description
Technical field
The present invention relates to a kind of title complex with anticancer activity [Ni (H
2l
2)
2] (H
2o)
2synthesis and application.
Background technology
Recent study finds that salicylic aldehyde Schiff bases title complex has good antibacterial, anti-inflammatory, the biological activity such as antitumor, the synthesis of salicylic aldehyde presence of Schiff-base complex and bioactive research thereof have become the important topic of pharmaceutical chemistry, biologist's research, for social development and technical progress play the effect become more and more important.Particularly in short supply present of efficient new drug, the medicine of exploitation tool high anti-cancer activity solves one of efficient new drug problem method in short supply.Title complex [Ni (H
2l
2)
2] (H
2o)
2there is unique biological activity, low toxicity that design and synthesis has the application prospect medicine such as antibacterial, antitumor efficiently can be used as, there is potential use.
Summary of the invention
Object of the present invention is exactly be design and synthesis title complex with anticancer activity [Ni (H
2l
2)
2] (H
2o)
2, utilize solvent structure title complex [Ni (H
2l
2)
2] (H
2o)
2and as the application of antitumor drug.
Title complex [Ni (the H that the present invention relates to
2l
2)
2] (H
2o)
2molecular formula be: C
26h
40n
2niO
10, molecular weight is: 599.29, and crystal structural data is in table one, and bond distance's bond angle data are in table two.Title complex [Ni (H
2l
2)
2] (H
2o)
2to human hepatoma cell strain (BEL-7404), human liver cancer cell (HepG2), cervical cancer cell (HeLa), human bladder cancer cell (T-24) and normal liver cell's strain (HL-7702) growth of tumour cell all have restraining effect, can apply as antitumor drug.
Table one: [Ni (H
2l
2)
2] (H
2o)
2crystallographic parameter
Table two: [Ni (H
2l
2)
2] (H
2o)
2bond distance
with bond angle (°)
Described title complex [Ni (H
2l
2)
2] (H
2o)
2synthetic method concrete steps be:
(1) analytically pure for 1.662g oxyethyl group salicylic aldehyde is placed in there-necked flask, the dehydrated alcohol heated and stirred adding 15ml treats that it dissolves completely, then the analytically pure 2-amino-2-methyl-1 of 1.051g is added, ammediol, add the dehydrated alcohol of 10ml again, heating in water bath, design temperature is 65 DEG C, return stirring about 120 minutes; The solution obtained cools under room temperature, crystallization of naturally volatilizing, and leaves standstill after 3 days, obtains yellow bulk crystals H
3l
2(H
3l
2=2-((3-oxyethyl group-2-phenol methylene) is amino)-2-methyl isophthalic acid, ammediol).
(2) by H that 0.128 gram of step (1) is synthesized
3l
215-20 ml volumes is dissolved in than being the dehydrated alcohol of 5:5 and making by oneself in the mixing solutions of distilled water with 0.249 gram of analytical pure four water nickelous acetate;
(3) solution obtained by step (2) is proceeded in the reactor of tetrafluoroethylene, react 120 hours at 80-90 DEG C, be cooled to room temperature, filter, filtrate is volatilized under being placed in room temperature crystallization naturally, obtains monocrystalline level title complex [Ni (H after 10 days
2l
2)
2] (H
2o)
2; Title complex [Ni (H is measured by single crystal diffractometer
2l
2)
2] (H
2o)
2structure.
The present invention has that technique is simple, with low cost, chemical composition is easy to control, reproducible and output advantages of higher.
Accompanying drawing explanation
Fig. 1 is part H of the present invention
3l
2enforcement figure.
Fig. 2 is title complex of the present invention [Ni (H
2l
2)
2] (H
2o)
2enforcement figure.
Fig. 3 is title complex of the present invention [Ni (H
2l
2)
2] (H
2o)
2structure iron.
Fig. 4 is title complex of the present invention [Ni (H
2l
2)
2] (H
2o)
2three-dimensional structure accumulation graph.
Embodiment
Embodiment:
Title complex [Ni (H
2l
2)
2] (H
2o)
2molecular formula be: C
26h
40n
2niO
10, molecular weight is: 599.29, and crystal structural data is in table one, and bond distance's bond angle data are in table two.
Title complex [Ni (H
2l
2)
2] (H
2o)
2synthetic method concrete steps be:
(1) analytically pure for 1.662g oxyethyl group salicylic aldehyde is placed in there-necked flask, the dehydrated alcohol heated and stirred adding 15ml treats that it dissolves completely, then the analytically pure 2-amino-2-methyl-1 of 1.051g is added, ammediol, add the dehydrated alcohol of 10ml again, heating in water bath, design temperature is 65 DEG C, return stirring about 120 minutes; The solution obtained cools under room temperature, crystallization of naturally volatilizing, and leaves standstill after 3 days, obtains yellow bulk crystals H
3l
2(H
3l
2=2-((3-oxyethyl group-2-phenol methylene) is amino)-2-methyl isophthalic acid, ammediol).
(2) by H that 0.128 gram of step (1) is synthesized
3l
215-20 ml volumes is dissolved in than being the dehydrated alcohol of 5:5 and making by oneself in the mixing solutions of distilled water with 0.249 gram of analytical pure four water nickelous acetate.
(3) solution obtained by step (2) is proceeded in the reactor of tetrafluoroethylene, react 120 hours at 80-90 DEG C, be cooled to room temperature, filter, filtrate is volatilized under being placed in room temperature crystallization naturally, obtains monocrystalline level title complex [Ni (H after 10 days
2l
2)
2] (H
2o)
2; Title complex [Ni (H is measured by single crystal diffractometer
2l
2)
2] (H
2o)
2structure.
Title complex with anticancer activity [Ni (H
2l
2)
2] (H
2o)
2the proliferation inhibition activity of various human tumor cell line is tested:
(1) cell strain and cell cultures:
Human hepatoma cell strain (BEL-7404) is selected in this experiment, human liver cancer cell (HepG2), cervical cancer cell (HeLa), human bladder cancer cell (T-24), 5 kinds of human cell lines such as normal liver cell's strain (HL-7702).All cells strain is all cultivated in the RPMI-1640 nutrient solution containing 10wt% calf serum, 100U/mL penicillin, 100U/mL Streptomycin sulphate, puts 37 DEG C containing volumetric concentration 5%CO
2cultivate in incubator.
(2) preparation of title complex to be measured:
{ [Ni (H used
2l
2)
2] (H
2o)
2purity>=95%, will its DMSO liquid storage physiological buffer dilute after be mixed with the whole solution of 20 μm of ol/L, wherein final concentration≤1% of solubility promoter DMSO, under testing this concentration, compound is to the suppression degree of various growth of tumour cell.
(3) cell growth inhibition test (mtt assay)
1) tumour cell of taking the logarithm vegetative period, after tryptic digestion, the cell suspension that concentration is 5000/ml is mixed with the nutrient solution containing 10% calf serum, be inoculated in 96 well culture plates with every hole 190 μ l, make hole, cell density to 1000 ~ 10000 to be measured (the aseptic PBS of marginal pore fills);
2) 5%CO
2, hatch 24h for 37 DEG C, be paved with at the bottom of hole to cell monolayer, every hole adds the medicine 10 μ L of finite concentration gradient, and each concentration gradient establishes 4 multiple holes;
3) 5%CO
2, hatch 48h for 37 DEG C, observe under inverted microscope;
4) every hole adds the MTT solution (5mg/mL PBS, i.e. 0.5%MTT) of 10 μ L, continues to cultivate 4h;
5) stop cultivating, carefully suck nutrient solution in hole, the DMSO that every hole adds 150 μ L fully dissolves first a ceremonial jade-ladle, used in libation precipitation, and after vibrator mixing, be 570nm at microplate reader wavelength, reference wavelength is the optical density value that 450nm measures each hole;
6) zeroing hole (substratum, MTT, DMSO) is set simultaneously, control wells (the medicine dissolution medium of cell, same concentrations, nutrient solution, MTT, DMSO).
7) according to the optical density value (OD value) recorded, judge viable cell quantity, OD value is larger, and cytoactive is stronger.Utilize formula:
Calculate the inhibiting rate of drug on tumor Growth of Cells, then calculate the IC of each test-compound to various human tumor cell line and Human normal hepatocyte strain respectively with Bliss method
50value.
Title complex [Ni (H
2l
2)
2] (H
2o)
2to human hepatoma cell strain (BEL-7404), the inhibiting rate of human liver cancer cell (HepG2), cervical cancer cell (HeLa), human bladder cancer cell (T-24) and normal liver cell's strain (HL-7702) growth of tumour cell in table three, to the IC of various human tumor cell line and Human normal hepatocyte strain
50value is in table four.
Table three: [Ni (H
2l
2)
2] (H
2o)
2to the inhibiting rate of different cell strain
| BEL-7404 | HepG2 | HeLa | T-24 | HL-7702 |
| 30.08±1.03 | 35.66±1.24 | 48.14±1.09 | 49.41±1.03 | 51.65±1.08 |
Table four: [Ni (H
2l
2)
2] (H
2o)
2to the half-inhibition concentration (IC of different cell strain
50, μM)
| BEL-7404 | HepG2 | HeLa | T-24 | HL-7702 |
| 39.81±1.02 | 25.42±1.48 | 19.06±1.03 | 19.44±1.05 | 18.536±1.06 |
Claims (2)
1. a title complex with anticancer activity [Ni (H
2l
2)
2] (H
2o)
2, it is characterized in that title complex [Ni (H
2l
2)
2] (H
2o)
2molecular formula be: C
26h
40n
2niO
10, molecular weight is: 599.29, title complex [Ni (H
2l
2)
2] (H
2o)
2have good antitumour activity, crystal structural data is in table one, and bond distance's bond angle data are in table two;
Described title complex [Ni (H
2l
2)
2] (H
2o)
2synthetic method concrete steps be:
(1) analytically pure for 1.662g oxyethyl group salicylic aldehyde is placed in there-necked flask, the dehydrated alcohol heated and stirred adding 15ml treats that it dissolves completely, then the analytically pure 2-amino-2-methyl-1 of 1.051g is added, ammediol, add the dehydrated alcohol of 10ml again, heating in water bath, design temperature is 65 DEG C, return stirring 120 minutes; The solution obtained cools under room temperature, crystallization of naturally volatilizing, and leaves standstill after 3 days, obtains yellow bulk crystals H
3l
2, H
3l
2for 2-((3-oxyethyl group-2-phenol methylene) is amino)-2-methyl isophthalic acid, ammediol;
(2) by H that 0.128 gram of step (1) is synthesized
3l
215-20 ml volumes is dissolved in than being the dehydrated alcohol of 5:5 and making by oneself in the mixing solutions of distilled water with 0.249 gram of analytical pure four water nickelous acetate;
(3) solution obtained by step (2) is proceeded in the reactor of tetrafluoroethylene, react 120 hours at 80-90 DEG C, be cooled to room temperature, filter, filtrate is volatilized under being placed in room temperature crystallization naturally, obtains monocrystalline level title complex [Ni (H after 10 days
2l
2)
2] (H
2o)
2; Title complex [Ni (H is measured by single crystal diffractometer
2l
2)
2] (H
2o)
2structure;
Table one: [Ni (H
2l
2)
2] (H
2o)
2crystallographic parameter
Table two: [Ni (H
2l
2)
2] (H
2o)
2bond distance
with bond angle (°)
2. title complex according to claim 1 [Ni (H
2l
2)
2] (H
2o)
2application, it is characterized in that title complex [Ni (H
2l
2)
2] (H
2o)
2apply as antitumor drug.
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|---|---|---|---|
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|---|---|---|---|
| CN201510071798.3A CN104650157A (en) | 2015-02-11 | 2015-02-11 | Synthesis method and application of a complex [Ni(H2L2)2](H2O)2 with anticancer activity |
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|---|---|
| CN104650157A true CN104650157A (en) | 2015-05-27 |
Family
ID=53241843
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|---|---|---|---|
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106188105A (en) * | 2016-09-13 | 2016-12-07 | 桂林理工大学 | Magnetic material salicylaldehyde derivatives Schiff's base copper complex ［ Cu4(hmdo)4h2o and synthetic method |
| CN106432362A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | 3-methoxy salicylaldehyde-2-amino-2-methyl-1,3-propanediol Schiff base nickel complex and synthesis method |
-
2015
- 2015-02-11 CN CN201510071798.3A patent/CN104650157A/en active Pending
Non-Patent Citations (4)
| Title |
|---|
| D.L.PENG: "Synthesis and crystal structures of manganese(Ⅳ) complexes with tridentate schiff bases", 《RUSSIAN JOURNAL OF COORDINATION CHEMISTRY》 * |
| ERNEST M. HODNETT等: "Schiff bases of salicylaldehyde and their cobalt(Ⅱ) derivatives as antitumor agents", 《PROCEEDINGS OF THE OKLAHOMA ACADEMY OF SCIENCE》 * |
| MISHTU DEY等: "Mono-, di- and tri-nuclear Ni(Ⅱ) complexes of N-, O-donor ligands: structural diversity and reactivity", 《INORGANIC CHEMISTRY COMMUNICATIONS》 * |
| 彭天良: "席夫碱过渡金属配合物的合成与结构", 《中国优秀硕士学位论文全文数据库ENGINEERING SCIENCE AND TECHNOLOGY Ⅰ》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106188105A (en) * | 2016-09-13 | 2016-12-07 | 桂林理工大学 | Magnetic material salicylaldehyde derivatives Schiff's base copper complex ［ Cu4(hmdo)4h2o and synthetic method |
| CN106432362A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | 3-methoxy salicylaldehyde-2-amino-2-methyl-1,3-propanediol Schiff base nickel complex and synthesis method |
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